CA2821392C - Composes cycliques indeno - Google Patents

Composes cycliques indeno Download PDF

Info

Publication number
CA2821392C
CA2821392C CA2821392A CA2821392A CA2821392C CA 2821392 C CA2821392 C CA 2821392C CA 2821392 A CA2821392 A CA 2821392A CA 2821392 A CA2821392 A CA 2821392A CA 2821392 C CA2821392 C CA 2821392C
Authority
CA
Canada
Prior art keywords
alkyl
alkoxy
substituted
mono
chosen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CA2821392A
Other languages
English (en)
Other versions
CA2821392A1 (fr
Inventor
Meng He
Anil Kumar
Darrin R. Dabideen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Transitions Optical Inc
Original Assignee
Transitions Optical Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Transitions Optical Inc filed Critical Transitions Optical Inc
Publication of CA2821392A1 publication Critical patent/CA2821392A1/fr
Application granted granted Critical
Publication of CA2821392C publication Critical patent/CA2821392C/fr
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D311/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/94Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D311/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78Ring systems having three or more relevant rings
    • C07D311/92Naphthopyrans; Hydrogenated naphthopyrans
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D451/00Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K9/00Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
    • C09K9/02Organic tenebrescent materials
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041Lenses
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00Optical elements other than lenses
    • G02B5/30Polarising elements
    • G02B5/3016Polarising elements involving passive liquid crystal elements
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00Photosensitive materials
    • G03C1/72Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
    • G03C1/73Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1003Carbocyclic compounds
    • C09K2211/1011Condensed systems
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1029Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1029Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1088Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00Optical elements other than lenses
    • G02B5/20Filters
    • G02B5/22Absorbing filters
    • G02B5/23Photochromic filters

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Pyrane Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Optical Filters (AREA)
  • Paints Or Removers (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne des composés représentés par les formules suivantes (I) et (II). Le cycle A des formules I et II peut être, par exemple, un groupe aryle, et Q' et Q''' peuvent chacun être indépendamment choisis parmi des groupes, tels que halogène, -OH, -CN, des groupes amine, des groupes amide, des groupes ester d'acide carboxylique, des groupes acide carboxylique, des groupes alcényle, des groupes alcynyle, des groupes carbonate, des groupes sulfure, et des groupes ester d'acide sulfonique. La présente invention concerne en outre des compositions photochromiques et des articles photochromiques qui comprennent un ou plusieurs composés photochromiques, tels que représentés par la formule II.
CA2821392A 2010-12-16 2011-12-01 Composes cycliques indeno Expired - Fee Related CA2821392C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US12/928,671 US20110140056A1 (en) 2003-07-01 2010-12-16 Indeno-fused ring compounds
US12/928,671 2010-12-16
PCT/US2011/062765 WO2012082381A1 (fr) 2010-12-16 2011-12-01 Composés cycliques indéno-condensés ayant des propriétés photochromiques

Publications (2)

Publication Number Publication Date
CA2821392A1 CA2821392A1 (fr) 2012-06-21
CA2821392C true CA2821392C (fr) 2016-06-14

Family

ID=45446173

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2821392A Expired - Fee Related CA2821392C (fr) 2010-12-16 2011-12-01 Composes cycliques indeno

Country Status (11)

Country Link
US (1) US20110140056A1 (fr)
EP (1) EP2651913B1 (fr)
JP (3) JP5890431B2 (fr)
KR (1) KR101610450B1 (fr)
AU (1) AU2011341472B2 (fr)
BR (1) BR112013014805B1 (fr)
CA (1) CA2821392C (fr)
ES (1) ES2632574T3 (fr)
MX (1) MX346746B (fr)
WO (1) WO2012082381A1 (fr)
ZA (1) ZA201304300B (fr)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8698117B2 (en) * 2003-07-01 2014-04-15 Transitions Optical, Inc. Indeno-fused ring compounds
US8211338B2 (en) 2003-07-01 2012-07-03 Transitions Optical, Inc Photochromic compounds
US8582192B2 (en) 2003-07-01 2013-11-12 Transitions Optical, Inc. Polarizing photochromic articles
US8623238B2 (en) 2008-06-27 2014-01-07 Transitions Optical, Inc. Mesogenic stabilizers
US8431039B2 (en) 2008-06-27 2013-04-30 Transitions Optical, Inc. Mesogenic stabilizers
US8613868B2 (en) 2008-06-27 2013-12-24 Transitions Optical, Inc Mesogenic stabilizers
US8349210B2 (en) 2008-06-27 2013-01-08 Transitions Optical, Inc. Mesogenic stabilizers
US9034219B2 (en) 2010-12-16 2015-05-19 Transitions Optical, Inc. Photochromic compounds and compositions
US8920928B2 (en) * 2010-12-16 2014-12-30 Transitions Optical, Inc. Photochromic compounds and compositions
US9029532B2 (en) * 2013-03-11 2015-05-12 Transitions Optical, Inc. 5,6-ring-substituted naphthopyran compounds
US9334439B2 (en) 2013-03-15 2016-05-10 Transitions Optical, Inc. Photochromic articles that include photochromic-dichroic materials
BR112017006502B1 (pt) 2014-09-30 2022-10-11 Transitions Optical, Inc Composto e elemento óptico
KR101818937B1 (ko) 2015-05-14 2018-01-18 (주)우노 앤 컴퍼니 퇴색속도가 매우 빠른 신규한 광변색성 물질
WO2018206096A1 (fr) 2017-05-10 2018-11-15 Transitions Optical, Ltd. Composés de phénanthréopyrane indéno-fusionnés photochromiques
WO2019001724A1 (fr) 2017-06-30 2019-01-03 Transitions Optical, Ltd. Composés photochromiques silole et germole à cycle fusionné
JP7195209B2 (ja) * 2018-04-17 2022-12-23 株式会社トクヤマ フォトクロミック化合物、該フォトクロミック化合物を含む硬化性組成物、及び該硬化性組成物からなるフォトクロミック硬化体
JP2023529241A (ja) 2020-06-01 2023-07-07 アイケアーズ メディカス インコーポレイテッド 両面非球面回折多焦点レンズ、その製造、および使用
JP7547510B2 (ja) * 2020-12-24 2024-09-09 ホヤ レンズ タイランド リミテッド フォトクロミック組成物、フォトクロミック物品及び眼鏡

Family Cites Families (120)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2475921A (en) * 1940-06-26 1949-07-12 Polaroid Corp Glare reduction filter comprising light polarizing area merging gradually with transparent nonpolarizing area
US2319826A (en) * 1941-10-10 1943-05-25 Gen Electric Adhesive composition
US2334446A (en) * 1941-12-26 1943-11-16 Polaroid Corp Polarizing goggles
US2481830A (en) * 1946-05-14 1949-09-13 Gen Polarizing Company Optically polarizing dichroic film and method of preparing the same
US2544659A (en) * 1946-05-14 1951-03-13 John F Dreyer Dichroic light-polarizing sheet materials and the like and the formation and use thereof
US3276316A (en) * 1961-08-02 1966-10-04 Polaroid Corp Process for polarizing ultraviolet light utilizing oriented polymer sheet with incorporated dichroic fluorescent dye
US3361706A (en) * 1964-03-06 1968-01-02 American Cyanamid Co Control of the photochromic return rate of (arylazo) thioformic arylhydrazidates
US3567605A (en) * 1966-03-30 1971-03-02 Ralph S Becker Photochemical process
GB1186987A (en) * 1967-08-30 1970-04-08 Fuji Photo Film Co Ltd Photochromic Compounds
US3653863A (en) * 1968-07-03 1972-04-04 Corning Glass Works Method of forming photochromic polarizing glasses
JPS4948631B1 (fr) * 1968-10-28 1974-12-23
US4043637A (en) * 1973-06-15 1977-08-23 American Optical Corporation Photochromic light valve
US4049338A (en) * 1974-11-19 1977-09-20 Texas Instruments Incorporated Light polarizing material method and apparatus
US4166043A (en) * 1974-12-23 1979-08-28 American Optical Corporation Stabilized photochromic materials
US4367170A (en) * 1975-01-24 1983-01-04 American Optical Corporation Stabilized photochromic materials
US4039254A (en) * 1976-05-27 1977-08-02 Mack Gordon Electro-optic welding lens assembly using multiple liquid crystal light shutters and polarizers
US4190330A (en) * 1977-12-27 1980-02-26 Bell Telephone Laboratories, Incorporated Variable focus liquid crystal lens system
US4215010A (en) * 1978-09-08 1980-07-29 American Optical Corporation Photochromic compounds
US4342668A (en) * 1978-09-08 1982-08-03 American Optical Corporation Photochromic compounds
US4279474A (en) * 1980-03-25 1981-07-21 Belgorod Barry M Spectacle lens having continuously variable controlled density and fast response time
US4720356A (en) * 1982-03-22 1988-01-19 American Optical Corporation Photochromic composition resistant to fatigue
FR2531235B1 (fr) * 1982-07-27 1985-11-15 Corning Glass Works Verres stratifies transparents polarisants et leur procede d'obtention
US4556605A (en) * 1982-09-09 1985-12-03 Kabushiki Kaisha Suwa Seikosha Photochromic coating composition and photochromic synthetic resin ophthalmic lens
US4637896A (en) * 1982-12-15 1987-01-20 Armstrong World Industries, Inc. Polymeric liquid crystals
US4685783A (en) * 1983-09-07 1987-08-11 The Plessey Company P.L.C. Polychromic tetracyclo-spiro-adamatylidene derivatives, and polychromic lens incorporating said compounds
US4637698A (en) * 1983-11-04 1987-01-20 Ppg Industries, Inc. Photochromic compound and articles containing the same
SE464264B (sv) * 1984-02-24 1991-03-25 Esab Ab Optiskt filter foer svetsskyddsglas
US4549894A (en) * 1984-06-06 1985-10-29 Corning Glass Works Ultraviolet absorbing photochromic glass of low silver content
FR2568568A1 (fr) * 1984-08-01 1986-02-07 Corning Glass Works Perfectionnement a la fabrication de verres stratifies transparents polarisants et verres ainsi obtenus
US4756605A (en) * 1985-02-01 1988-07-12 Olympus Optical Co., Ltd. Liquid crystal spectacles
AU564689B2 (en) * 1985-07-09 1987-08-20 Kureha Kagaku Kogyo K.K. Photochromic lens
FR2590889B1 (fr) * 1985-08-13 1988-01-22 Corning Glass Works Perfectionnements a la fabrication de verres stratifies transparents polarisants et verres ainsi obtenus
DE3531923A1 (de) * 1985-09-07 1987-03-12 Bayer Ag Verfahren zur herstellung von 1-aminonaphthalin-2,4,7-trisulfonsaeure und 1-aminonaphthalin-7-sulfonsaeure
US4880667A (en) * 1985-09-24 1989-11-14 Ppg Industries, Inc. Photochromic plastic article and method for preparing same
US4810433A (en) * 1985-09-25 1989-03-07 Fuji Photo Film Co., Ltd. Process for producing oriented film
IT1190508B (it) * 1986-03-24 1988-02-16 Daniele Senatore Occhiali a trasparenza regolabile
GB8611837D0 (en) * 1986-05-15 1986-06-25 Plessey Co Plc Photochromic spiropyran compounds
GB8614680D0 (en) * 1986-06-17 1986-07-23 Plessey Co Plc Photoreactive lenses
US4785097A (en) * 1986-09-26 1988-11-15 Ppg Industries, Inc. Method for synthesizing spiro-oxazines
US4816584A (en) * 1986-11-12 1989-03-28 Ppg Industries, Inc. Photochromic spiro(indoline)benzoxazines
CA1340939C (fr) * 1987-02-02 2000-03-28 Ryojiro Akashi Compose photochromique
US4838673A (en) * 1987-04-27 1989-06-13 J. R. Richards, Inc. Polarized lens and method of making the same
JP2578442B2 (ja) * 1987-07-13 1997-02-05 三菱化学株式会社 分子配向性薄膜
US4931219A (en) * 1987-07-27 1990-06-05 Ppg Industries, Inc. Photochromic compound and articles containing the same
DE3879024T2 (de) * 1987-07-31 1993-10-07 Takeda Chemical Industries Ltd Pyridinium-Derivate, ihre Herstellung und Verwendung.
US4873029A (en) * 1987-10-30 1989-10-10 Blum Ronald D Method for manufacturing lenses
US5180524A (en) * 1987-11-05 1993-01-19 Enichem Synthesis S.P.A. Photochromatic composition and photochromatic articles which contain it
US4931220A (en) * 1987-11-24 1990-06-05 Ppg Industries, Inc. Organic photochromic pigment particulates
NL8802832A (nl) * 1988-02-29 1989-09-18 Philips Nv Methode voor het vervaardigen van een gelaagd element en het aldus verkregen element.
DE3814631A1 (de) * 1988-04-29 1989-11-09 Rodenstock Optik G Photochrome substanzen (iv)
US5130058A (en) * 1988-07-01 1992-07-14 Tokuyama Soda Kabushiki Kaisha Photochromic compound, process for production thereof, use thereof and composition containing said photochromic compound
DE3825066A1 (de) * 1988-07-23 1990-01-25 Roehm Gmbh Verfahren zur herstellung von duennen, anisotropen schichten auf oberflaechenstrukturierten traegern
US4931221A (en) * 1988-12-30 1990-06-05 Ppg Industries, Inc. Photochromic spiropyran compounds
US4974941A (en) * 1989-03-08 1990-12-04 Hercules Incorporated Process of aligning and realigning liquid crystal media
FR2647789B1 (fr) * 1989-06-05 1994-07-22 Essilor Int Composes photochromiques de type indolino-spiro-oxazine, leur procede de preparation, compositions et articles photochromiques contenant de tels composes
US5180470A (en) * 1989-06-05 1993-01-19 The Regents Of The University Of California Deposition of highly-oriented PTFE films and uses therefor
DE69023865T2 (de) * 1989-07-28 1996-10-17 Wako Pure Chem Ind Ltd Fulgimidderivate.
JP2692290B2 (ja) * 1989-08-31 1997-12-17 ソニー株式会社 ディスク記録及び/又は再生装置
US5186867A (en) * 1989-12-12 1993-02-16 Enichem Synthesis, S.P.A. Spiro-indoline oxazine compounds with photochromatic and photosensitizing characteristics and the process for their preparation
US5130353A (en) * 1990-03-07 1992-07-14 Ppg Industries, Inc. Method for preparing photochromic plastic article
US5073294A (en) * 1990-03-07 1991-12-17 Hercules Incorporated Process of preparing compositions having multiple oriented mesogens
US5185390A (en) * 1990-03-07 1993-02-09 Ppg Industries, Inc. Water strippable photochromic resin composition
US5066818A (en) * 1990-03-07 1991-11-19 Ppg Industries, Inc. Photochromic naphthopyran compounds
JPH063528B2 (ja) * 1990-03-16 1994-01-12 富士ゼロックス株式会社 光変調表示素子及び表示方法
JP2811353B2 (ja) * 1990-07-06 1998-10-15 ゼリア新薬工業株式会社 炎症性腸疾患予防・治療剤
US5200116A (en) * 1990-07-23 1993-04-06 Ppg Industries, Inc. Photochromic chromene compounds
JPH04199024A (ja) * 1990-11-29 1992-07-20 Hitachi Ltd 液晶表示素子およびそれを用いた表示装置
US5202053A (en) * 1991-02-22 1993-04-13 Hercules Incorporated Polymerizable nematic monomer compositions
SG50596A1 (en) * 1991-07-26 2001-01-16 Rolic Ag Photo-oriented polymer networks and method of their manufacture
US5189448A (en) * 1991-08-08 1993-02-23 Katsumi Yaguchi Unit for searching for a lost contact lens
US5608567A (en) * 1991-11-05 1997-03-04 Asulab S.A. Variable transparency electro-optical device
EP0543678A1 (fr) * 1991-11-22 1993-05-26 Nippon Oil Company, Limited Procédé de production d'éléments optiques résistants à la chaleur
US5644416A (en) * 1991-11-26 1997-07-01 Fuji Xerox Co., Ltd. Light modulation device and method of light modulation using the same
US5289547A (en) * 1991-12-06 1994-02-22 Ppg Industries, Inc. Authenticating method
US5238981A (en) * 1992-02-24 1993-08-24 Transitions Optical, Inc. Photochromic naphthopyrans
JP3016533B2 (ja) * 1992-03-03 2000-03-06 株式会社トクヤマ フォトクロミック組成物
EP0587280B1 (fr) * 1992-07-14 1997-02-26 Mitsui Petrochemical Industries, Ltd. Matériau composite de liquide cristallin anti-ferro-électrique, procédé pour sa préparation et élément de liquide cristallin l'utilisant
US5274132A (en) * 1992-09-30 1993-12-28 Transitions Optical, Inc. Photochromic naphthopyran compounds
US5405958A (en) * 1992-12-21 1995-04-11 Transitions Optical, Inc. Photochromic spiro(indoline)naphthoxazine compounds
DE59403063D1 (de) * 1993-02-17 1997-07-17 Hoffmann La Roche Optisches Bauelement
EP0622789B1 (fr) * 1993-03-30 2002-08-07 Bayer Ag Structures encouche contenant des polymères à chaíne latérale
IT1264563B1 (it) * 1993-06-09 1996-10-04 Enichem Sintesi Composti fotocromatici e metodo per la loro preparazione
US5384077A (en) * 1993-06-21 1995-01-24 Transitions Optical, Inc. Photochromic naphthopyran compounds
US5466398A (en) * 1993-06-21 1995-11-14 Transitions Optical, Inc. Photochromic substituted naphthopyran compounds
KR970000356B1 (ko) * 1993-09-18 1997-01-08 엘지전자 주식회사 액정표시소자(lcd)용 광 폴리머 배향막 형성방법
DE4434966A1 (de) * 1994-09-30 1996-04-04 Bayer Ag Neue Seitengruppenpolymere und ihre Verwendung für optische Bauelemente
US5645767A (en) * 1994-11-03 1997-07-08 Transitions Optical, Inc. Photochromic indeno-fused naphthopyrans
US5658501A (en) * 1995-06-14 1997-08-19 Transitions Optical, Inc. Substituted naphthopyrans
US5746949A (en) * 1995-11-21 1998-05-05 Hoechst Celanese Corp. Polarizer films comprising aromatic liquid crystalline polymers comprising dichroic dyes in their main chains
AU710875B2 (en) * 1995-12-06 1999-09-30 Tokuyama Corporation Chromene compounds and photochromic materials
DE19651286A1 (de) * 1995-12-20 1997-06-26 Rodenstock Optik G Photochrome 3H-Naphthopyrane
US5744070A (en) * 1995-12-20 1998-04-28 Transitions Optical, Inc. Photochromic substituted naphthopyran compounds
US5723072A (en) * 1996-06-17 1998-03-03 Ppg Industries, Inc. Photochromic heterocyclic fused indenonaphthopyrans
US5955520A (en) 1996-06-17 1999-09-21 Ppg Industries, Inc. Photochromic indeno-fused naphthopyrans
US5698141A (en) * 1996-06-17 1997-12-16 Ppg Industries, Inc. Photochromic heterocyclic fused indenonaphthopyrans
US5869658A (en) 1997-12-15 1999-02-09 Ppg Industries, Inc. Photochromic indeno-fused naptho 2,1-b!pyrans
US6555028B2 (en) 1998-09-11 2003-04-29 Transitions Optical, Inc. Polymeric matrix compatibilized naphthopyrans
AU761180B2 (en) 1998-09-11 2003-05-29 Transitions Optical, Inc Polymerizable polyalkoxylated naphthopyrans
US5961892A (en) 1998-09-11 1999-10-05 Ppg Industries Ohio, Inc. Polyalkoxylated naphthopyrans
US6068797A (en) 1998-12-11 2000-05-30 Ppg Industries Ohio, Inc. Method of preparing a shaped article having a photochromic coating thereon
US6296785B1 (en) * 1999-09-17 2001-10-02 Ppg Industries Ohio, Inc. Indeno-fused photochromic naphthopyrans
WO2001034609A1 (fr) 1999-11-10 2001-05-17 Optische Werke G. Rodenstock Derives indenochromes heterocycliquement anneles
JP4157245B2 (ja) * 2000-02-21 2008-10-01 株式会社トクヤマ クロメン化合物
DE50103963D1 (en) 2000-06-07 2004-11-11 Rodenstock Gmbh Photochrome pyranderivate
US6736998B2 (en) 2000-12-29 2004-05-18 Transitions Optical, Inc. Indeno-fused photochromic naphthopyrans
US7008568B2 (en) 2001-11-20 2006-03-07 Vision-Ease Lens, Inc. Photochromic naphthopyran compounds: compositions and articles containing those naphthopyran compounds
US7320826B2 (en) 2003-03-20 2008-01-22 Ppg Industries Ohio, Inc. Photochromic articles with reduced temperature dependency and methods for preparation
US7262295B2 (en) * 2003-03-20 2007-08-28 Transitions Optical, Inc. Indeno-fused photochromic naphthopyrans, naphthols and photochromic articles
US7166357B2 (en) 2003-03-20 2007-01-23 Transitions Optical, Inc. Photochromic articles that activate behind ultraviolet radiation blocking transparencies and methods for preparation
US8545984B2 (en) * 2003-07-01 2013-10-01 Transitions Optical, Inc. Photochromic compounds and compositions
US7342112B2 (en) * 2003-07-01 2008-03-11 Ppg Industries Ohio, Inc. Photochromic compounds
US8211338B2 (en) 2003-07-01 2012-07-03 Transitions Optical, Inc Photochromic compounds
US8698117B2 (en) * 2003-07-01 2014-04-15 Transitions Optical, Inc. Indeno-fused ring compounds
US8518546B2 (en) * 2003-07-01 2013-08-27 Transitions Optical, Inc. Photochromic compounds and compositions
JP4663523B2 (ja) * 2003-09-18 2011-04-06 株式会社トクヤマ クロメン化合物
US20060228557A1 (en) * 2005-04-08 2006-10-12 Beon-Kyu Kim Photochromic materials having extended pi-conjugated systems and compositions and articles including the same
US8748634B2 (en) * 2006-10-30 2014-06-10 Transitions Optical, Inc. Photochromic materials demonstrating improved fade rates
JP2009067754A (ja) * 2007-09-14 2009-04-02 Tokuyama Corp クロメン化合物
US8859097B2 (en) * 2010-12-16 2014-10-14 Transitions Optical, Inc. Photochromic compounds, compositions and articles
US8920928B2 (en) * 2010-12-16 2014-12-30 Transitions Optical, Inc. Photochromic compounds and compositions

Also Published As

Publication number Publication date
US20110140056A1 (en) 2011-06-16
BR112013014805B1 (pt) 2018-06-12
CA2821392A1 (fr) 2012-06-21
JP2015044860A (ja) 2015-03-12
JP5890431B2 (ja) 2016-03-22
ZA201304300B (en) 2014-12-23
KR101610450B1 (ko) 2016-04-07
JP2014506245A (ja) 2014-03-13
MX346746B (es) 2017-03-28
JP2015078206A (ja) 2015-04-23
WO2012082381A1 (fr) 2012-06-21
EP2651913A1 (fr) 2013-10-23
BR112013014805A2 (pt) 2016-07-19
ES2632574T3 (es) 2017-09-14
AU2011341472B2 (en) 2015-07-09
EP2651913B1 (fr) 2017-04-19
AU2011341472A1 (en) 2013-07-04
KR20130112924A (ko) 2013-10-14
MX2013006925A (es) 2013-07-22
CN103339123A (zh) 2013-10-02

Similar Documents

Publication Publication Date Title
CA2821392C (fr) Composes cycliques indeno
JP5852137B2 (ja) インデノ縮合環化合物
CA2914571C (fr) Composes photochromiques
EP2970326B1 (fr) Composés de naphtopyrane substitué à cycle condensé en position 5,6
EP3071576A1 (fr) Composés photochromiques pyrane à cycle condensé indéno
CN103339123B (zh) 具有光致变色性质的茚并稠环化合物

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20130612

MKLA Lapsed

Effective date: 20201201